Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus

Abstract

Provided is an electrophotographic photosensitive member, including in the following order: a support; a charge-generating layer; and a charge-transporting layer, in which: the charge-generating layer includes a gallium phthalocyanine crystal in which an organic compound is contained; the organic compound is at least one compound selected from the group consisting of dimethyl sulfoxide, N,N-dimethylformamide, N-methylformamide, N-propylformamide, N-vinylformamide, and N-methylpyrrolidone; a content of the organic compound is 0.1% by mass or more and 1.5% by mass or less with respect to a mass of gallium phthalocyanine in the gallium phthalocyanine crystal; and the charge-transporting layer comprises at least one compound selected from the group consisting of a compound represented by the formula (1), a compound represented by the formula (2), a compound represented by the formula (3), and a compound represented by the formula (4).

What is claimed is: 
     
         1 . An electrophotographic photosensitive member, comprising in the following order:
 a support;   a charge-generating layer; and   a charge-transporting layer, wherein:   the charge-generating layer comprises a gallium phthalocyanine crystal in which an organic compound is contained;   the organic compound is at least one compound selected from the group consisting of dimethyl sulfoxide, N,N-dimethylformamide, N-methylformamide, N-propylformamide, N-vinylformamide, and N-methylpyrrolidone;   a content of the organic compound is 0.1% by mass or more and 1.5% by mass or less with respect to a mass of gallium phthalocyanine in the gallium phthalocyanine crystal; and   the charge-transporting layer comprises at least one compound selected from the group consisting of a compound represented by the formula (1), a compound represented by the formula (2), a compound represented by the formula (3), and a compound represented by the formula (4):   
       
         
           
           
               
               
           
         
       
       in the formula (1):
 Ar 1  and Ar 2  each independently represent a substituted or unsubstituted phenyl group; 
 X represents a phenylene group; 
 Y 1  and Y 2  each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzyl group, a 9,9-dimethyl-9H-fluoren-2-yl group, or a group represented by the following formula (A); 
 a substituent of the substituted phenyl group is an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, or a phenyl group; and 
 a substituent of the substituted benzyl group is a methyl group or an ethyl group, 
 
       
         
           
           
               
               
           
         
       
       in the formula (A):
 Ar 3  represents a substituted or unsubstituted phenyl group; 
 a substituent of the substituted phenyl group is an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, or a phenyl group; 
 R 1  represents a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms; and 
 a substituent of the substituted alkyl group is an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, or a phenyl group, 
 
       
         
           
           
               
               
           
         
       
       in the formula (2):
 Ar 101  to Ar 104  each independently represent a substituted or unsubstituted aryl group, 
 
       
         
           
           
               
               
           
         
       
       in the formula (3):
 Ar 105  to Ar 110  each independently represent a substituted or unsubstituted aryl group; and 
 Ar 111  represents a phenylene group or a 4,4′-biphenyldiyl group, 
 
       
         
           
           
               
               
           
         
       
       in the formula (4):
 Ar 112  to Ar 117  each independently represent a substituted or unsubstituted aryl group; 
 Ar 118  and Ar 119  each independently represent a phenylene group or a 4,4′-biphenyldiyl group; and 
 R 101  and R 102  each independently represent an alkyl group or a phenyl group, or R 101  and R 102  represent groups necessary for forming a ring structure by being bonded to each other together with a carbon atom to which R 101  and R 102  are bonded. 
 
     
     
         2 . An electrophotographic photosensitive member according to  claim 1 , wherein a content of the organic compound is 0.4% by mass or more and 1.4% by mass or less with respect to a mass of gallium phthalocyanine in the gallium phthalocyanine crystal. 
     
     
         3 . An electrophotographic photosensitive member according to  claim 1 , wherein the organic compound is at least one compound selected from the group consisting of N-methylformamide, N-propylformamide, and N-vinylformamide. 
     
     
         4 . An electrophotographic photosensitive member according to  claim 1 , wherein Y 1  in the formula (1) represents a 9,9-dimethyl-9H-fluoren-2-yl group. 
     
     
         5 . An electrophotographic photosensitive member according to  claim 4 , wherein Y 1  and Y 2  in the formula (1) each represent a 9,9-dimethyl-9H-fluoren-2-yl group. 
     
     
         6 . An electrophotographic photosensitive member according to  claim 1 , wherein Ar 1  and Ar 2  in the formula (1) each represent a tolyl group. 
     
     
         7 . An electrophotographic photosensitive member according to  claim 1 , wherein at least one of Ar 101  to Ar 104 , at least one of Ar 105  to Ar 110 , and at least one of Ar 112  to Ar 117  in the formulae (2) to (4) each represent a 9,9-dimethyl-9H-fluoren-2-yl group. 
     
     
         8 . An electrophotographic photosensitive member according to  claim 7 , wherein Ar 105  and Ar 106  in the formula (3) each represent a 9,9-dimethyl-9H-fluoren-2-yl group. 
     
     
         9 . An electrophotographic photosensitive member according to  claim 7 , wherein Ar 112  and Ar 113  in the formula (4) each represent a 9,9-dimethyl-9H-fluoren-2-yl group and R 101  and R 102  in the formula (4) each represent a methyl group. 
     
     
         10 . An electrophotographic photosensitive member according to  claim 1 , wherein the gallium phthalocyanine crystal is a hydroxygallium phthalocyanine crystal. 
     
     
         11 . An electrophotographic photosensitive member according to  claim 1 , wherein the gallium phthalocyanine crystal is a chlorogallium phthalocyanine crystal. 
     
     
         12 . A process cartridge, which integrally supports an electrophotographic photosensitive member and at least one device selected from the group consisting of a charging device, a developing device, a transferring device and a cleaning device, and is detachably mountable to a main body of an electrophotographic apparatus, wherein:
 the electrophotographic photosensitive member comprises in the following order:
 a support; 
 a charge-generating layer; and 
 a charge-transporting layer, 
   the charge-generating layer comprises a gallium phthalocyanine crystal in which an organic compound is contained;   the organic compound is at least one compound selected from the group consisting of dimethyl sulfoxide, N,N-dimethylformamide, N-methylformamide, N-propylformamide, N-vinylformamide, and N-methylpyrrolidone;   a content of the organic compound is 0.1% by mass or more and 1.5% by mass or less with respect to a mass of gallium phthalocyanine in the gallium phthalocyanine crystal; and   the charge-transporting layer comprises at least one compound selected from the group consisting of a compound represented by the formula (1), a compound represented by the formula (2), a compound represented by the formula (3), and a compound represented by the formula (4):   
       
         
           
           
               
               
           
         
       
       in the formula (1):
 Ar 1  and Ar 2  each independently represent a substituted or unsubstituted phenyl group; 
 X represents a phenylene group; 
 Y 1  and Y 2  each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzyl group, a 9,9-dimethyl-9H-fluoren-2-yl group, or a group represented by the following formula (A); 
 a substituent of the substituted phenyl group is an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, or a phenyl group; and 
 a substituent of the substituted benzyl group is a methyl group or an ethyl group, 
 
       
         
           
           
               
               
           
         
       
       in the formula (A):
 Ar 3  represents a substituted or unsubstituted phenyl group; 
 a substituent of the substituted phenyl group is an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, or a phenyl group; 
 R 1  represents a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms; and 
 a substituent of the substituted alkyl group is an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, or a phenyl group, 
 
       
         
           
           
               
               
           
         
       
       in the formula (2):
 Ar 101  to Ar 104  each independently represent a substituted or unsubstituted aryl group, 
 
       
         
           
           
               
               
           
         
       
       in the formula (3):
 Ar 105  to Ar 110  each independently represent a substituted or unsubstituted aryl group; and 
 Ar 111  represents a phenylene group or a 4,4′-biphenyldiyl group, 
 
       
         
           
           
               
               
           
         
       
       in the formula (4):
 Ar 112  to Ar 117  each independently represent a substituted or unsubstituted aryl group; 
 Ar 118  and Ar 119  each independently represent a phenylene group or a 4,4′-biphenyldiyl group; and 
 R 101  and R 102  each independently represent an alkyl group or a phenyl group, or R 101  and R 102  represent groups necessary for forming a ring structure by being bonded to each other together with a carbon atom to which R 101  and R 102  are bonded. 
 
     
     
         13 . An electrophotographic apparatus, comprising:
 an electrophotographic photosensitive member;   a charging device;   an exposing device;   a developing device; and   a transferring device, wherein:   the electrophotographic photosensitive member comprises in the following order:
 a support; 
 a charge-generating layer; and 
 a charge-transporting layer, 
   the charge-generating layer comprises a gallium phthalocyanine crystal in which an organic compound is contained;   the organic compound is at least one compound selected from the group consisting of dimethyl sulfoxide, N,N-dimethylformamide, N-methylformamide, N-propylformamide, N-vinylformamide, and N-methylpyrrolidone;   a content of the organic compound is 0.1% by mass or more and 1.5% by mass or less with respect to a mass of gallium phthalocyanine in the gallium phthalocyanine crystal; and   the charge-transporting layer comprises at least one compound selected from the group consisting of a compound represented by the formula (1), a compound represented by the formula (2), a compound represented by the formula (3), and a compound represented by the formula (4):   
       
         
           
           
               
               
           
         
       
       in the formula (1):
 Ar 1  and Ar 2  each independently represent a substituted or unsubstituted phenyl group; 
 X represents a phenylene group; 
 Y 1  and Y 2  each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzyl group, a 9,9-dimethyl-9H-fluoren-2-yl group, or a group represented by the following formula (A); 
 a substituent of the substituted phenyl group is an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, or a phenyl group; and 
 a substituent of the substituted benzyl group is a methyl group or an ethyl group, 
 
       
         
           
           
               
               
           
         
       
       in the formula (A):
 Ar 3  represents a substituted or unsubstituted phenyl group; 
 a substituent of the substituted phenyl group is an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, or a phenyl group; 
 R 1  represents a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms; and 
 a substituent of the substituted alkyl group is an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, or a phenyl group, 
 
       
         
           
           
               
               
           
         
       
       in the formula (2):
 Ar 101  to Ar 104  each independently represent a substituted or unsubstituted aryl group, 
 
       
         
           
           
               
               
           
         
       
       in the formula (3):
 Ar 105  to Ar 110  each independently represent a substituted or unsubstituted aryl group; and 
 Ar 111  represents a phenylene group or a 4,4′-biphenyldiyl group, 
 
       
         
           
           
               
               
           
         
       
       in the formula (4):
 Ar 112  to Ar 117  each independently represent a substituted or unsubstituted aryl group; 
 Ar 118  and Ar 119  each independently represent a phenylene group or a 4,4′-biphenyldiyl group; and 
 R 101  and R 102  each independently represent an alkyl group or a phenyl group, or R 101  and R 102  represent groups necessary for forming a ring structure by being bonded to each other together with a carbon atom to which R 101  and R 102  are bonded.